Hydrochloric Acid → HCID 23324906, compound

HRID 464735Notes

Reaction equation

HRID 464735 reaction equation
C[O:2][C:3](=[O:22])[CH2:4][CH2:5][CH:6]1[CH:10]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)[CH2:9][C:8](=[O:21])[NH:7]1.C[O:24][C:25](=[O:44])[CH2:26][CH:27]([C:34]1[CH:39]=[CH:38][C:37]([C:40]([F:43])([F:42])[F:41])=[CH:36][CH:35]=1)[CH:28]1[CH2:32][CH2:31][C:30](=[O:33])[NH:29]1.Cl>[OH-].[Na+]>[O:33]=[C:30]1[NH:29][CH:28]([CH:27]([C:34]2[CH:39]=[CH:38][C:37]([C:40]([F:43])([F:41])[F:42])=[CH:36][CH:35]=2)[CH2:26][C:25]([OH:44])=[O:24])[CH2:32][CH2:31]1.[O:21]=[C:8]1[NH:7][CH:6]([CH2:5][CH2:4][C:3]([OH:22])=[O:2])[CH:10]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:18])[F:19])=[CH:13][CH:12]=2)[CH2:9]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 54256950HCID 54256950, compoundHCID 54267983HCID 54267983, compound

Product 2

HCID 23324906HCID 23324906, compoundHCID 23324907HCID 23324907, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of 93.4 g of 5-oxo-3-[4-(trifluoromethyl)phenyl]-2-pyrrolidinepropanoic acid methyl ester and 5-oxo-β-[4-(trifluoromethyl)phenyl]-2-pyrrolidinepropanoic acid methyl ester in 370 ml of 1 N aqueous sodium hydroxide solution is heated to 60° C. for four hours. Excess aqueous hydrochloric acid (1 N, 380 ml) is added and the solution concentrated under reduced pressure to give 5-oxo-β-[4-(trifluoromethyl)phenyl]-2-pyrrolidinepropanoic acid and 5-oxo-3-[4-(trifluoromethyl)phenyl]-2-pyrrolidinepropanoic acid. The acids are dissolved in 300 ml of acetic anhydride, and the solution is heated to 90° C. The solution is filtered hot and the filtrate concentrated in vacuo. The oil is chromatographed on silica gel (200-400 mesh) (elution with chloroform) to give cis-and trans-dihydro-1-(4-trifluoro-methylphenyl)-1H-pyrrolizine-3,5-(2H,6H)-diones as a white solid with a mp 173°-181° C.

Workup

  1. concentrationthe solution concentrated under reduced pressure

Sources & evidence

ORD record
ord-10e5774165d341388e0c77af859721a5
Source dataset
uspto-grants-1985_10
Patent number
US04548947

Reaction notes

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